Pharmaceutical compounds.



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.rtlnenlv CALLSEN, or ELBERFELD, GERMANY. ASSIGNOR r FARBENFABRIKEN vom/r. rnrnen. BAYER & 00., or ELBERFELD, GERMANY, A CORPORATION or Patented Apr. 21, 1914.

GERMAITY.

PHARMACEUTICAL COMPOUNDS.

lldll 'dfllllge Specification of Letters Patent.

No Drawing.

To all whom it may concern:

Be it known that l, Jfmoen CALLsnN, doctor of philosophy, chemist, citizen of the German Empire, residing at Elberiield, Germany, have invented new and useful Improvements in Pharmaceutical Compounds, of which the following isv a specification.

My invention relates to the'production of new pharmaceutical products, which are chemically alkoxymcthyl esters of cresotinic acids having the following general formula:

CO.O.CH-1.OR

R meaning an alkyl radical, such as methyl, ethyl, propyl or the like) and which, according to my researches, possess valuable therapeutic properties, being good remedies against rheumatism, an average dose being between 3 and 10 grams for external application.

llhe process for producing my new compounds consists in treating salts of cresotinic acids with halogenmethyl alkylethers having the following general formula:

XiCH,-UR (X meaning a halogen atom, It meaning an allryl radical).

The new products are colorless liquids soluble in ether, alcohol, chloroform and Their alcoholic solutions are colbenzene. ored violet by ferric chlorid.

In carrying out my new process practically, I can proceed as follows, the parts being by weight :To 1'74 parts of the dry sodium salt df meta-cresotinic acid 80.5

parts. of monochlorodimethylether having the formula CH,C1- 0 CH,

are added little by little, taking care that the temperature does not rise above C. The mixture is stirred for 2 hours. The reaction will be completed after 12 hours. The reaction mass is then treated with a dilute solution of sodium carbonate in order to remove the sodium chlorid and the excess of cresotinic acid. The resulting oil is sepaltpplication filed June 17, 1913. Serial No. 774,125.

rated from the salt solution, washed until neutral, dried by means of chlorid of calmum and distilled in cacao. The resulting mlethoxymethyl cresotinate having the formu a:

COO.CH=.OCH

is a clear almost odorless liquid boiling at l25-181 C. under a ressure of about 5 mm. On being heated at the ordinary pressure formic aldehyde is split ofif When. treated with dilute acids it breaks up into cresotinic acid, formic aldehyde and methylic alcohol.

The process proceeds in an analogous manner if other halogenmethylalkylethers be used. The ethoxymethybmeta-cresotinic ester boils at 130-135 C, .under a'pressure of about'lO mm. Other cresotinic acids, such as the para or ortho-cresotinic acids may be used- 1. The new alkoxymethyl esters of cresotinic acids of the following general formula:

being ,a clear odorless liquid boiling at 125 13? 0. under a iess'fire of about 5 m y hand in the presence of two subscribing IfIlIIL, brelzzlkggdup igto mfitai-creiotilnilc afid, wltnesses.

Ormic a e e an met y 10a 00 0 W1en reacted upon yby dilute acids and eit'hibiting JURGEN CALLSEN' 5 valuable therapeutic properties, substan- Witnesses: tially as described. HELEN NUFER.

' "In testimonywhereof I have hereunto set ALBERT N UFER. 

